Functionalized materials and compounds

Patent metadata

Field	Value
Publication number	US-11192883-B2
Application number	US-201917288122-A
Country	US
Kind code	B2
Filing date	Oct 25, 2019
Priority date	Oct 26, 2018
Publication date	Dec 7, 2021
Grant date	Dec 7, 2021

Abstract

Processes for chemical functionalization of materials is described. The processed generally include chemical reaction between a thiol group of a first compound or material and an alkane group or alkyne group of a second compound or material. Also disclosed are functionalized materials and compounds suitable for functionalizing a material.

First claim

The invention claimed is:

1. A process for chemical functionalization wherein the process includes reacting an alkene compound of the formula

wherein m is an integer between 1 and 22 inclusive with a thiol reactant at the thiol moiety thereof, said thiol reactant selected from the group consisting of a thiol-containing compound and a material that comprises a pendant thiol moiety.

2. The process of claim 1 wherein said alkene compound has the formula:

3. The process of claim 1 wherein said thiol reactant is a material that comprises a pendant thiol moiety.

4. The process of claim 1 further comprising forming said material that comprises a pendant thiol moiety, said forming step comprising chemically modifying a material essentially devoid of pendant thiol moieties to include a pendant thiol moiety.

5. The process of claim 4 wherein said chemically modifying step comprises reacting a material comprising pendant amino, amido, imino or hydroxyl groups with cyanuric chloride or a derivative thereof.

6. The process of claim 1 wherein thiol reactant is a thiol-containing compound.

7. The process of claim 6 further comprising the step of forming said thiol-containing compound, said forming step comprising reacting a compound of the formula

wherein R is selected from the group consisting of H, alkyl, alkenyl and aromatic groups and m is an integer between 1 and 22 inclusive
with cyanuric chloride or a derivative thereof to form said thiol-containing compound.

8. The process of claim 7 wherein said compound of the formula

wherein R is selected from the group consisting of H, alkyl, alkenyl and aromatic groups and m is an integer between 1 and 22 inclusive
is cysteamine.

9. The process of claim 6 further comprising the step of covalently bonding the reaction product of said thiol-containing compound and said alkene from said reacting step to a material comprising pendant amino, amido, imino or hydroxyl groups.

10. The process of claim 6 further comprising the step of forming said thiol-containing compound, said forming step comprising reacting cysteine with cyanuric chloride or a derivative thereof.

11. A process for chemical functionalization, said process comprising reacting a thiol compound of the formula:

wherein m is an integer between 1 and 22 inclusive;

with an alkene reactant at the alkene moiety thereof, said alkene reactant selected from the group consisting of an alkene-containing compound or a material that comprises a pendant alkene moiety.

12. The process of claim 11 wherein said thiol compound has the formula

13. The process of claim 11 wherein said alkene reactant is a material that comprises a pendant alkene moiety.

14. The process of claim 13 further comprising a step of forming said material that comprises a pendant alkene moiety, said forming step comprising chemically modifying a material essentially devoid of pendant alkene moieties to include a pendant alkene moiety.

15. The process of claim 14 wherein said chemically modifying step comprises reacting a material comprising pendant amino, amido, imino or hydroxyl groups with cyanuric chloride or a derivative thereof.

16. The process of claim 11 wherein said alkene reactant is an alkene-containing compound.

17. The process of claim 16 further including the step of forming said alkene-containing compound, said forming step comprising reacting a compound of the formula

wherein R is selected from the group consisting of H, aryl, alkenyl and aromatic groups and m is an integer between 1 and 22 inclusive
with cyanuric chloride or a derivative thereof to form said alkene-containing compound.

18. The process of claim 16 further comprising the step of covalently bonding the reaction product of said alkene-containing compound and said thiol compound from said reacting step to a material comprising pendant amino, amido, imino or hydroxyl groups.

19. A compound suitable for functionalizing a material comprising pendant amino, amido, imino or hydroxyl groups, said compound having the formula:

Wherein Y and Z are each independently selected from the group consisting of Cl, OH and NH 2 .

Assignees

• Univ South Alabama

Inventors

• Glover Thomas Grant
• West Kevin N

Classifications

• D06M13/165

  Ethers (D06M13/11 takes precedence) · CPC title

• C07D233/74 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members · CPC title

• D06M2101/06

  cellulosic · CPC title

• C07D251/40

  Nitrogen atoms · CPC title

• C07D403/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title